The invention relates to novel substituted phenyluracils and novel intermediates for their preparation and to their use as herbicides.
Certain substituted aryluracils are already known from the (patent) literature (cf. EP-A-255047, EP-A-260621, EP-A-408382, EP-A-438209, EP-A-473551, EP-A-517181, EP-A-563384, WO-A-91/00278, WO-A-91/07393, WO-A-93/14073, WO-A-98/41093, U.S. Pat. No. 4,979,982, U.S. Pat. No. 5,084,084, U.S. Pat. No. 5,127,935, U.S. Pat. No. 5,154,755, U.S. Pat. No. 5,169,430, U.S. Pat. No. 5,486,610, U.S. Pat. No. 5,356,863). However, these compounds have hitherto not attained any particular importance.
This invention, accordingly, provides novel substituted phenyluracils of the general formula (I) 
in which
n represents the numbers 0, 1 or 2,
R1 represents hydrogen, amino or optionally substituted alkyl,
R2 represents carboxyl, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted alkyl or alkoxycarbonyl,
X represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, phenylcarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkinyl, alkinyloxy or alkinyloxycarbonylxe2x80x94where in the case that n is greater than 1, X in the individual possible compounds may also have meanings other than those given.
In the definitions, the hydrocarbon chains, such as alkyl, are in each case straight-chain or branchedxe2x80x94including in combination with heteroatoms, such as in alkoxy.
If the compounds of the general formula (I) according to the invention contain substituents with asymmetric carbon atoms, the invention relates in each case to the R enantiomers and the S enantiomers, and to any mixtures of these enantiomers, in particular the racemates.
n preferably represents the numbers 1 or 2.
R1 preferably represents hydrogen, amino or optionally cyano-, carboxyl-, fluorine-, chlorine-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted C1-C4-alkyl.
R2 preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl or in each case optionally fluorine-substituted C1-C4-alkyl or C1-C4-alkoxy-carbonyl.
X preferably represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, represents in each case optionally hydroxyl-, cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-, C1-C4-alkylsulphonyl-, C1-C4-alkyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C2-C4-alkenyl-oxycarbonyl-, C2-C4-alkinyl-oxycarbonyl-, C1-C4-alkylamino-carbonyl-, di-(C1-C4-alkyl)-amino-carbonyl-, phenoxycarbonyl-, benzyloxy-carbonyl-, phenylaminocarbonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6 carbon atoms, represents dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano-, fluorine-, chlorine-, bromine- or C1-C4-alkoxy-substituted alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy or alkylaminocarbonyloxy having in each case 1 to 6 carbon atoms in the alkyl groups, represents dialkylaminocarbonyl or dialkylaminocarbonyloxy having in each case 1 to 6 carbon atoms in the alkyl groups, represents phenylcarbonyloxy, represents in each case optionally fluorine-, chlorine- or bromine-substituted alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino having in each case up to 6 carbon atoms, or represents in each case optionally cyano-, carboxyl-, fluorine-, chlorine-, bromine- or C1-C4-alkoxy-carbonyl-substituted alkenyl, alkenyloxy, alkenyloxycarbonyl, alkinyl, alkinyloxy or alkinyloxycarbonyl having in each case up to 6 carbon atoms.
n particularly preferably represents the number 1.
R1 particularly preferably represents hydrogen, amino or methyl.
R2 particularly preferably represents carboxyl, cyano, carbamoyl, methoxycarbonyl or trifluoromethyl.
X particularly preferably represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, allyloxycarbonyl-, 1-buten-3-yloxycarbonyl-, 2-buten-4-yl-oxycarbonyl-, propargyloxycarbonyl-, 1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, represents dimethylamino or diethylamino, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, n- or i-butylaminocarbonyloxy, represents dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy or diethylaminocarbonyloxy, represents n- or i-butylcarbonyloxy, represents phenylcarbonyloxy, represents in each case optionally fluorine- or chlorine-substituted acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, n-, i-, s- or t-butylsulphonylamino, or represents in each case optionally cyano-, carboxyl-, fluorine-, chlorine-, methoxycarbonyl- or ethoxycarbonyl-substituted ethenyl, propenyl, propenyloxy, propenyloxycarbonyl, ethinyl, propinyl, propinyloxy or propinyloxycarbonyl.
X very particularly preferably represents hydroxyl, mercapto, amino, represents in each case cyano-, carboxyl-, carbamoyl-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, n-, i-, s- or t-butoxycarbonyl-, allyloxycarbonyl-, 1-buten-3-yloxycarbonyl-, 2-buten-4-yloxycarbonyl-, propargyloxycarbonyl-, 1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted methyl, methoxy, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, represents in each case cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, allyloxycarbonyl-, 1-buten-3-yloxycarbonyl-, 2-buten-4-yl-oxycarbonyl-, propargyloxycarbonyl-, 1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted n-, i-, s- or t-butoxy, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, represents dimethylamino or diethylamino, represents in each case cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methoxycarbonyl or ethoxycarbonyl, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted acetyl, propionyl, n- or i-butyroyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, n- or i-butylaminocarbonyloxy, represents dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy or diethylaminocarbonyloxy, represents n- or i-butylcarbonyloxy, represents phenylcarbonyloxy, represents in each case optionally fluorine- or chlorine-substituted acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, n-, i-, s- or t-butylsulphonylamino, or represents in each case optionally cyano-, carboxyl-, fluorine-, chlorine-, methoxycarbonyl- or ethoxycarbonyl-substituted ethenyl, propenyl, propenyloxy, propenyloxycarbonyl, ethinyl, propinyl, propinyloxy or propinyloxycarbonyl.
X most preferably represents in each case cyano-, carboxyl-, carbamoyl-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, allyloxycarbonyl-, 1-buten-3-yloxycarbonyl-, 2-buten-4-yloxycarbonyl-, propargyloxycarbonyl-, 1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl- (and optionally additionally fluorine- or chlorine-) substituted methyl, ethyl, n-propyl, n-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, represents acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy or phenylcarbonyloxy, represents n- or i-butylcarbonyloxy, represents dimethylamino, n- or i-butylaminocarbonyloxy, or represents in each case cyano-, carboxyl-, methoxycarbonyl- or ethoxycarbonyl- (and optionally additionally fluorine- or chlorine-) substituted ethenyl, propenyl, propenyloxy, ethinyl, propinyl or propinyloxy.
Preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.
Particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
Very particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.
Most preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being most preferred.
A very particularly preferred group are the compounds of the formula (I) 
in which
n represents 1 or 2,
R1 represents hydrogen or methyl,
R2 represents trifluoromethyl, carbamoyl, carboxyl, methoxycarbonyl or cyano, and
X represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, allyloxycarbonyl-, propargyloxycarbonyl-, 1-buten-3-yloxycarbonyl-, 2-buten-4-yloxycarbonyl-, propargyloxycarbonyl-, 1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl or ethoxycarbonyl, or represents methoxycarbonyl- or ethoxycarbonyl-substituted ethenyl, or
X represents in each case cyano-, carboxyl-, carbamoyl-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, allyloxycarbonyl-, 1-buten-3-yl-oxycarbonyl-, 2-buten-4-yloxycarbonyl-, propargyloxycarbonyl-, 1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl- (and optionally additionally fluorine- or chlorine-) substituted methyl, ethyl, n-propyl, n-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, represents acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy or phenylcarbonyloxy, represents n- or i-butylcarbonyloxy, represents dimethylamino, n- or i-butylaminocarbonyloxy, or represents in each case cyano-, carboxyl-, methoxycarbonyl- or ethoxycarbonyl- (and optionally additionally fluorine- or chlorine-) substituted ethenyl, propenyl, propenyloxy, ethinyl, propinyl or propinyloxy.
A further very particularly preferred group are those compounds of the formula (I) in which
n represents 1 or 2,
R1 represents methyl,
R2 represents trifluoromethyl, carbamoyl, carboxyl, cyano or methoxycarbonyl, and
X has one of the meanings given above for compounds of the formula (I).
A further very particularly preferred group are those compounds of the formula (I) in which
n represents 1 or 2,
R1 represents hydrogen,
R2 represents trifluoromethyl, carbamoyl, carboxyl, cyano or methoxycarbonyl, and
X has one of the meanings given above for compounds of the formula (I).
A further very particularly preferred group are those compounds of the formula (I) in which
n represents 1 or 2,
R1 represents hydrogen or methyl,
R2 represents trifluoromethyl, and
X has one of the meanings given above for compounds of the formula (I).
A further very particularly preferred group are those compounds of the formula (IA) 
in which
R1 represents hydrogen or methyl,
R2 represents trifluoromethyl, and
X represents in each case carboxyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl- or phenylaminocarbonyl-substituted methyl, ethyl, methoxy, ethoxy, or
X represents n- or i-butylaminocarbonyloxy, n- or i-butylcarbonyloxy, dimethylamino, methoxycarbonyloxy, ethoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, or represents dimethylaminocarbonyloxy.
A further very particularly preferred group are those compounds of the formula (IA) in which
R1 represents hydrogen or methyl,
R2 represents trifluoromethyl, and
X represents in each case carboxyl-, methoxycarbonyl- or ethoxycarbonyl-substituted methyl, methoxy or ethoxy, or
X represents methoxycarbonyloxy, ethoxycarbonyloxy, methylaminocarbonyloxy or ethylaminocarbonyloxy.
The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another at will, i.e. including combinations between the given preferred ranges.
Examples of the compounds of the general formula (I) according to the invention are listed in the groups below.
Group 1
X1 has here the meanings given in the list below:
4-(1-carboxy)-ethoxy, 4-(1-ethoxycarbonyl)-ethoxy, 3-(1-ethoxycarbonyl)-ethoxy, 3-ethoxycarbonylmethoxy, 2-(1-ethoxycarbonyl)-ethoxy.
Group 2
X1 represents dimethylaminocarbonylmethoxy or methylaminocarbonylmethoxy and
X2 represents methyl.
Group 3
X1 represents phenylaminocarbonylethoxy or phenylaminocarbonylmethoxy.
Group 4
X1 represents n- or i-butylcarbonyloxy or ethoxycarbonyloxy.
Group 5
X1 represents 4-ethylaminocarbonyloxy, 4-(n- or i-)butylaminocarbonyloxy, 3-methylaminocarbonyloxy or 2-methylaminocarbonyloxy.
Group 6
X1 represents dimethylamino and
R1 represents hydrogen or methyl.
Group 7
X1 represents 2-chloro, 3-chloro, 4-chloro, 3-fluoro, 4-fluoro, 3-methyl, 3-cyano, 4-cyano, 2-methylthio, 2-methylsulphinyl or 4-methylsulphinyl.
Group 8
X1 represents 2-chloro, 3-chloro, 4-chloro, 2-fluoro, 4-fluoro, 3-methyl, 3-nitro, 4-methyl, 3-cyano, 4-cyano, 2-methylthio, 4-nitro, 2-cyano, 4-methylthio or 2-methoxy.
Group 9
Xn represents (3,4-)Cl2 or (2,4-)F2.
Group 10
Xn represents (3,4-)Cl2 or (2,4-)F2.
Group 11
X1 represents hydroxyl or methoxy, and
X2 represents methyl.
Group 12
X1 represents 4-methoxy, 3-chloro or 4-cyano.
Group 13
X1 represents 3-trifluoromethyl, 4-chloro, 3-methoxy, 3-chloro or 4-cyano.
Group 14
X1 represents 3-methoxy, 3-chloro or 4-cyano.
Group 15
X1 represents 3-trifluoromethyl, 4-chloro, 3-methoxy, 3-chloro or 4-cyano.
Group 16
R2 represents methoxycarbonyl, carbamoyl or cyano.
Group 17
R2 represents carbamoyl or cyano.
The novel substituted phenyluracils of the general formula (I) have interesting biological properties. In particular, they have strong herbicidal activity.
The novel substituted phenyluracils of the general formula (I) are obtained when
(a) halogenophenyluracils of the general formula (II) 
xe2x80x83in which
R1 and R2 are each as defined above and
X3 represents halogen,
are reacted with aryl compounds of the general formula (III) 
xe2x80x83in which
n and X are each as defined above,
or with metal salts of compounds of the general formula (III),
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(b) aminoalkenoic esters of the general formula (I) 
xe2x80x83in which
R2 is as defined above and
R represents alkyl, aryl or arylalkyl,
are reacted with aryl isocyanates of the general formula (V) 
xe2x80x83in which
n and X are each as defined above,
or with arylurethanes (arylcarbamates) of the general formula (VI) 
xe2x80x83in which
n and X are each as defined above and
R represents alkyl, aryl or arylalkyl,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(c) N-aryl-1-alkoxycarbonylamino-maleimides of the general formula (VII) 
xe2x80x83in which
n and X are each as defined above and
Rxe2x80x2 represents alkyl,
are reacted with a metal hydroxide in the presence of water and, if appropriate, in the presence of an organic solvent,
or when
(d) substituted phenyluracils of the general formula (Ia) 
xe2x80x83in which
n and X are each as defined above
are reacted with 1-aminooxy-2,4-dinitro-benzene or with alkylating agents of the general formula (VIII)
X4xe2x80x94A1 (VIII)
xe2x80x83in which
A1 represents optionally substituted alkyl and
X4 represents halogen or the grouping xe2x80x94Oxe2x80x94SO2xe2x80x94Oxe2x80x94A1,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and electrophilic or nucleophilic and/or oxidation or reduction reactions within the scope of the definition of the substituents are, if appropriate, subsequently carried out in a customary manner.
The compounds of the general formula (I) can be converted by customary methods into other compounds of the general formula (I) according to the above definition, for example by esterification or hydrolysis (for example X: OCH2COOHxe2x86x92OCH2COOC2H5, OCH(CH3)COOCH3xe2x86x92OCH(CH3)COOH), conversion of carboxyl compounds into other carboxylic acid derivatives by customary methods (for example R2: COOHxe2x86x92CN, CNxe2x86x92CSNH2, COOHxe2x86x92COOCH3, COOCH3xe2x86x92CONH2); cf. the Preparation Examples).
Using, for example, 1-(4-cyano-2,5-difluoro-phenyl)-4-chlorodifluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine and ethyl 1(4-hydroxy-phenoxy)-propionate as starting materials, the course of the reaction in the process (a) according to the invention can be illustrated by the following reaction scheme: 
Using, for example, methyl 3-amino-4,4,4-trifluoro-crotonate and 4-cyano-2-fluoro-5-phenoxy-phenyl isocyanate as starting materials, the course of the reaction in process (b) according to the invention can be illustrated by the following reaction scheme: 
Using, for example, methyl [1-(4-cyano-2-fluoro-5-phenoxy-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-carbamate as starting material, the course of the reaction in the process (c) according to the invention can be illustrated by the following reaction scheme: 
Using, for example, 1-[2-fluoro-4-cyano-5-(4-methoxycarbonylmethoxy-phenoxy)-phenyl]-4-difluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine and methyl bromide as starting materials, the course of the reaction in the process (d) according to the invention can be illustrated by the following reaction scheme: 
The formula (II) provides a general definition of the halogenophenyluracils to be used as starting materials in the process (a) according to the invention for preparing compounds of the formula (I). In the formula (II), R1 and R2 each in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred, particularly preferred or very particularly preferred for R1 and R2; X3 preferably represents fluorine or chlorine, in particular fluorine.
The starting materials of the general formula (II) are known and/or can be prepared by processes known per se (cf. EP-A-648749).
The formula (III) provides a general definition of the aryl compounds further to be used as starting materials in the process (a) according to the invention. In the formula (III), n and X each in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred, particularly preferred or very particularly preferred for n and X.
The starting materials of the general formula (III) are known organic chemicals for synthesis.
The formula (IV) provides a general definition of the aminoalkenoic esters to be used as starting materials in the process (b) according to the invention for preparing compounds of the general formula (I). In the general formula (IV), R2 in particular has that meaning which has already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred or very particularly preferred for R2; R preferably represents C1-C4-alkyl, phenyl or benzyl, in particular methyl or ethyl.
The starting materials of the general formula (IV) are known and/or can be prepared by processes known per se (cf. J. Heterocycl. Chem. 9 (1972), 513-522).
The formula (V) provides a general definition of the aryl isocyanates further to be used as starting materials in the process (b) according to the invention. In the general formula (V), n and X each in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred or very particularly preferred for n and X.
The novel aryl isocyanates of the general formula (V) are obtained when aniline derivatives of the general formula (IX) 
in which
n and X are each as defined above,
are reacted with phosgene in the presence of a diluent, such as, for example, chlorobenzene, at temperatures between xe2x88x9220xc2x0 C. and +150xc2x0 C. (cf., for example, also EP-A-648749).
The formula (VI) provides a general definition of the arylurethanes to be used, if appropriate, as starting materials in the process (b) according to the invention. In the general formula (VI), n and X each in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred or very particularly preferred for n and X; R preferably represents C1-C4-alkyl, phenyl or benzyl, in particular methyl or ethyl.
The novel arylurethanes of the general formula (VI) are obtained when aniline derivatives of the general formula (IX) 
in which
n and X are each as defined above,
are reacted with chlorocarbonyl compounds of the general formula (X)
ROxe2x80x94COxe2x80x94Clxe2x80x83xe2x80x83(X)
xe2x80x83in which
R is as defined above,
if appropriate in the presence of an acid acceptor, such as, for example, pyridine, and if appropriate in the presence of a diluent, such as, for example, methylene chloride, at temperatures between xe2x88x9220xc2x0 C. and +100xc2x0 C. (cf. the Preparation Examples).
The aniline derivatives of the general formula (IX) required as precursors have hitherto not been disclosed.
The aniline derivatives of the general formula (IX) 
xe2x80x83in which
n and X are each as defined above,
are obtained when anilines of the general formula (XI) 
xe2x80x83in which
X3 is as defined above,
are reacted with phenols of the general formula (III) 
xe2x80x83in which
n and X are each as defined above,
or with metal salts of compounds of the general formula (III),
if appropriate in the presence of a reaction auxiliary, such as, for example, sodium hydride, and if appropriate in the presence of a diluent, such as, for example, N-methylpyrrolidone, at temperatures between 0xc2x0 C. and 150xc2x0 C. (cf. the Preparation Examples).
The formula (VII) provides a general definition of the N-aryl-1-alkoxycarbonyl-amino-maleimides to be used as starting materials in the process (c) according to the invention for preparing compounds of the general formula (I). In the general formula (VII), n and X each in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred or very particularly preferred for n and X; Rxe2x80x2 preferably represents C1-C4-alkyl, in particular methyl or ethyl.
The N-aryl-1-alkoxycarbonylamino-maleimides of the general formula (VII) are obtained when alkyl (2,5-dioxo-2,5-dihydro-furan-3-yl)-carbamates of the general formula (XII) 
in which
Rxe2x80x2 represents alkyl (in particular methyl or ethyl),
are reacted with aniline derivatives of the general formula (IX) 
xe2x80x83in which
n and X are each as defined above,
if appropriate in the presence of a diluent such as, for example, acetic acid, at temperatures between 0xc2x0 C. and 200xc2x0 C., preferably between 50xc2x0 C. and 150xc2x0 C.
The precursors of the general formula (XII) are known and/or can be prepared by processes known per se (cf. DE 19604229).
The formula (Ia) provides a general definition of the substituted phenyluracils to be used as starting materials in the process (d) according to the invention for preparing compounds of the formula (I). In the formula (Ia), n and X each in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred, particularly preferred or very particularly preferred for n and X.
The starting materials of the general formula (Ia) for process (d) can be prepared by the processses (a), (b) and (c) according to the invention.
The formula (VIII) provides a general definition of the alkylating agents further to be used as starting materials in the process (d) according to the invention. In the formula (VIII), A1 preferably represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl having 1 to 4 carbon atoms and X2 represents chlorine, bromine, iodine, methylsulphonyloxy or ethylsulphonyloxy: in particular, A1 represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl and X2 represents chlorine, bromine, iodine, methylsulphonyloxy or ethylsulphonyloxy.
The starting materials of the formula (VIII) are known organic chemicals for synthesis.
The processes according to the invention for preparing the compounds of the general formula (I) are preferably carried out using diluents. Suitable diluents for carrying out the processes (a), (b), (c) and (d) according to the invention are, in addition to water, especially inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate, sulphoxides, such as dimethyl sulphoxide, alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water or pure water.
Suitable reaction auxiliaries for the processes (a), (b), (c) and (d) according to the invention are, in general, the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, such as, for example, sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide, or potassium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or butoxide; furthermore also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N,N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N,N-dimethyl-aniline, N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo[2.2.2]-octane, (DABCO), 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).
Suitable further reaction auxiliaries for the processses according to the invention are also phase-transfer catalysts. Examples of such catalysts which may be mentioned are:
Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulphate, methyl-trioctylammonium chloride, hexadecyl-trimethylammonium chloride, hexadecyl-trimethylammonium bromide, benzyl-trimethylammonium chloride, benzyl-triethylammonium chloride, benzyl-trimethylammonium hydroxide, benzyl-triethylammonium hydroxide, benzyl-tributylammonium chloride, benzyl-tributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributyl-hexadecylphosphonium bromide, butyl-triphenylphosphonium chloride, ethyl-trioctylphosphonium bromide, tetraphenylphosphonium bromide.
When carrying out the processes (a), (b), (c) and (d) according to the invention the reaction temperatures can be varied within a relatively wide range. In general, the processes are carried out at temperatures between 0xc2x0 C. and 150xc2x0 C., preferably between 10xc2x0 C. and 120xc2x0 C.
The processes according to the invention are generally carried out under atmospheric pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressurexe2x80x94in general between 0.1 bar and 10 bar.
For carrying out the processes according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess of one of the components. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for several hours. Work-up is carried out by customary methods (cf. the Preparation Examples).
The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed killers. By weeds in the broadest sense there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The active compounds according to the invention can be used, for example, in connection with the following plants:
Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants. Depending on the concentration, the compounds are suitable for total weed control, for example on industrial terrain and rail tracks and on paths and areas with and without tree growth. Equally, the compounds can be employed for controlling weeds in perennial crops, for example forests, ornamental tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns and turf and pastures and for selective weed control in annual crops.
The compounds of the formula (I) according to the invention have strong herbicidal activity and a broad activity spectrum when used on the soil and above-ground parts of plants. To a certain extent, they are also suitable for selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both by the pre-emergence and by the post-emergence method.
The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic substances impregnated with active compound, and microencapsulations in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is to say liquid solvents and/or solid carriers, optionally with the use of surfactants, that is to say emulsifiers and/or dispersants and/or foam formers.
If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Liquid solvents which are mainly suitable are: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and water.
Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic meals, and granules of organic material, such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates; suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.
Tackifiers, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils.
It is possible to use colorants, such as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.
Possible components for the mixtures are known herbicides, for example acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl), benfuresate, bensulfuron(-methyl), bentazon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl), chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlortoluron, cinidon(-ethyl), cinmethylin, cinosulfuron, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethacblor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl), ethoflimesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop(-P-ethyl), flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl), flazasulfuron, fluazifop(-P-butyl), fluazolate, flucarbazone, flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam, flupropacil, flurpyrsulfuron(-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr(-meptyl), flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen, glufosinate(-ammonium), glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl), haloxyfop(-P-methyl), hexazinone, imazamethabenz-(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosuIlfumn, iodosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlorbole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor, metosulam, metoxuron, metribuzin, metsulfuron(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasuilfron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac(-methyl), pyrithiobac(-sodium), quinchlorac, quimnerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuiron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.
A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, is also possible.
The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering.
The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing.
The amount of active compound used can vary within a relatively wide range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.
The preparation and the use of the active compounds according to the invention can be seen from the examples below.